Hydrochlorid of orthodioxy-phenyl-ethanol-methylamin in a crystallized form.



UNlTED STATES PATENT OFFICE.

FRANZ FLAECHER, OF HOCHST-ON-THE-MAIN, GERMANY, ASSIGNOR TO H. A. METZ &

00., OF NEW YORK, N. Y., A CORPORATION OF NEW YORK. I

HYDROCHLORID OF OR'IHODIOXY-PHENYL-ETHANOL-METHYLAMIN IN A CRYSTAL- LIZED Specification of Letters Patent.

No Drawing. Application filed April 17, '1908.

To all whom "it may concern:

Be it known that l, FRANZ FLAECIIER, Ph. I chcz'nist, citizen of the Empire of (tin-litany, and residing at I-liichst-on-the- Main, Germany, have invented certain new and useful l mproven'ients in the Manufacture of the ll"tl]'0Cl'llO1l(l of Orthodioxy- Phenyl- Ethanollvlethylamin in a Crystallized Form, of which the following is a speei tieati on.

All experiments to obtain crystallized salts of ort'hod ioXy-phenyl-ethanolmethylauiin which in the market under the name 01 Supmrenine or Adrenaline, have hitherto been unsuccessful (compare '1. ifJ. 'lalcauiine, Chem inches Uc'ntralblatt 1901. ll. S. 1354:). The base itself is insoluble, therefore it has been brought on the market in a hydrocl'iloric solution. This so lution had however the disadvantage that it was relatively unstable and that it could be used only it preservative agents were added. A. salt of the ortlrodioxy-phenyL ethanolmethylan'iin, being entirely stable in air, crystallizing and readily and neutrally soluble in water, would be of great therapeutical value.

I have now :t'ound that the hydrochlorid of the base will be obtained in nice crystals and in agood yield, it synthetic orthodioxy phenyl ethanoln'iethylamin (compare Patent No. 930,703) is treated with alc0- holic h "drochloric acid.

llxauiple: ()ne molecule of orthodioxyphenyl-et'hauolu'iethylalnin is moistened thoroughly with some quantity of absolute alcohol and dissolved in the theoretically required quantity oil? alcoholic hydrochloric arid. For instance. lSi-l (1 molecule) of orthodioxy-phenyl-ethanol-inethylamin are moistened with some alcohol and then dissolved in one u'ioleeule 146 gr. of 25 per cent. absolute alcoholic hydrochloric acid. The reaction involved corresponds to the formula:

After a short, time, especially after l re-- queut. stirring with the glass-rod, the liquid crystallizes. The crystals are filtered,

FORM.

Patented Sept. 12. 1911.

Serial No. 427,674. (Specimens) washed with absolute alcohol and ether and recrystallized from alcohol. The crystals are in the form of rhon'ibic prisms.

'lhe hydrochlorid orthodioXy-phenylethanolinethylan in obtained thereby is colorless readily soluble in water with neutral reaction and difficulty soluble in absolute alcohol. 1t melts at 161 C., and is optically inactive.

Having now what I claim is:

1. The process for the manufacture of hydrochlorid ot' orthodioxyphenyl-ethanolmethyhimin in a crystallized form, which consists in treating the optically inactive base with alcoholic hydrochloric acid and allowing it to crystallize.

2. The herein described process of pro dueing in crystallized form an optically in active substance having the astringent and hemostatic properties of the suprarenaL glands, consisting in moistcning an optically inactive base of said substance thoroughly with absolut alcohol, dissolving the same in alcoholic hydrochloric acid, and allowing it to crystallize.

3. As a new product substance possessin heinostatie properti gland, consisting of c: n'less crystals, stable in air, readily soluble in water with a neutral reaction, ditiieultly soluble in absolute alcohol, and having melting point at 161 degrees C.

a. As a new prodlut, the crystallized hydroehlorid of orthoalioxyphenylethanolmethylamin in the form of rhombic prisms, which are stable in air, colorless, readily soluble in water with neutral reaction, di ticultly soluble in absolute alcohol, having a. melting point of 16,? degrees (1., and the aqueous solution of the salt being optically inactive.

In testimony, that 1 claim the foregoing as my invention, I have signed my name in presence of two subscribing witnesses.

FRANZ FLAECHER.

described my invention,

Witnesses:

JEAN GRUND,

CARL GRUND. 

